Synthesis of a Fluorogenic Cyclooctyne Activated by Cu-Free Click Chemistry

被引：83
|
作者：
Jewett, John C.
Bertozzi, Carolyn R. [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 22期
基金：
美国国家卫生研究院;
关键词：
STAUDINGER LIGATION; LIVING CELLS; COPPER-FREE; CYCLOADDITIONS; MODULATION; PROBE;
D O I：
10.1021/ol2025026
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclooctyne-based probes that become fluorescent upon reaction with azides are important targets for real-time imaging of azide-labeled biomolecules. The concise synthesis of a coumarin-conjugated cyclooctyne, coumBARAC, that undergoes a 10-fold enhancement in fluorescence quantum yield upon triazole formation with organic azides is reported. The design principles embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited for biological imaging.
引用
收藏
页码：5937 / 5939
页数：3
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